3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: 3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester
• CAS No.: 89193-18-0
• Molecular Formula: C14H16N2O2
• Molecular Weight: 244.293
• DSSTox Substance ID: DTXSID90349672
• Nikkaji Number: J2.142.339D
• Wikidata: Q82125069
• Pharos Ligand ID: PPK85NUD4P35
• ChEMBL ID: CHEMBL1794670
• Mol file: 89193-18-0.mol

Synonyms:3,5-DIMETHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER;89193-18-0;ethyl 3,5-dimethyl-1-phenylpyrazole-4-carboxylate;1H-Pyrazole-4-carboxylic acid, 3,5-dimethyl-1-phenyl-, ethyl ester;1y2c;Pyrazole carboxylic ester 8;3DE;SCHEMBL6069548;CHEMBL1794670;BDBM14785;DTXSID90349672;BUIZDUYEIRRDAV-UHFFFAOYSA-N;MFCD00233461;AKOS000320108;AB05031;AS-5831;PD038437;ETHYL 3,5-DIMETHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE;3,5-DIMETHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLICACIDETHYLESTER

Chemical Property of 3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 290

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N(N=C1C)C2=CC=CC=C2)C

Technology Process of 3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester

There total 12 articles about 3,5-Dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-acetyl-3-aminobut-2-enoic acid ethyl ester (26682-94-0) + phenylhydrazine (100-63-0) → 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester (89193-18-0)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; at 20 ℃; for 2h; regioselective reaction; Reflux;

DOI:10.1039/b820324e

Reference yield: 95.0%

ethyl 2-acetyl-3-ethoxybut-2-enoate (99181-91-6) + phenylhydrazine (100-63-0) → 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester (89193-18-0)

Guidance literature:

In ethanol; at -10 ℃; for 2h;

Reference yield: 78.0%

ethyl acetoacetate (141-97-9) + aniline (62-53-3) + acetonitrile (75-05-8,26809-02-9) → 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester (89193-18-0)

Guidance literature:

ethyl acetoacetate; aniline; With indium(III) bromide; at 20 ℃; for 1h; Inert atmosphere; neat (no solvent);

acetonitrile; With copper diacetate; at 110 ℃; for 24h;

DOI:10.1002/anie.201002389

upstream raw materials:

2,4-dimethyl-5-nitro-6-oxo-6H-pyran-3-carboxylic acid ethyl ester

acetic acid

phenylhydrazine

ethyl 3-(2-phenylhydrazono)butanoate

Downstream raw materials:

3,5-dimethyl-1-phenyl-1H-pyrazole-4-carboxylic acid

2,3,5-trimethyl-1-phenylpyrazolium-4-carboxylate

4-hydroxy-3,5-dimethyl-1-phenylpyrazole